Methanol → HCID 54674656, compound

HRID 2402752Notes

Reaction equation

HRID 2402752 reaction equation
BrC1C=CC(S([O:11][C@H:12]2[C@@H:19]3[C@@H:15]([CH2:16][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=4)[CH2:18]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[CH3:30]O>>[CH3:30][O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([CH2:16][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=3)[CH2:18]2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 887MethanolHCID 86659290HCID 86659290, compound

Product 1

HCID 54674656HCID 54674656, compound

Procedure

(3aR,4R,6aS)-2-[6-(Trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl 4-bromobenzenesulfonate (100 mg, 0.204 mmol) from Example 39 was heated at 85° C. for 3 days in methanol (0.3 mL) to give a colorless solution. The methanol was removed in vacuo, and the crude material was purified by silica gel chromatography using 100% dichloromethane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.57-7.53 (m, 1H), 7.01 (d, J=7.3, 1H), 6.54 (d, J=8.6, 1H), 3.58 (dd, J=11.0, 8.8, 1H), 3.52 (dd, J=7.1, 4.8, 1H), 3.47 (dd, J=10.7, 7.8, 1H), 3.28 (dd, J=11.1, 4.8, 1H), 3.24-3.18 (m, 4H), 2.81-2.64 (m, 2H), 1.93 (dq, J=12.9, 7.9, 1H), 1.80 (dtd, J=13.2, 7.8, 5.4, 1H), 1.68 (ddd, J=17.7, 11.3, 6.7, 1H), 1.38-1.25 (m, 1H); MS (ESI+) m/z 287 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customThe methanol was removed in vacuo
  3. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-225007bef7734d95a7e74754788974fa
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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